4-Acetyl-N-(4-nitrobenzylidene)aniline | 20534-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Acetyl-N-(4-nitrobenzylidene)aniline
• 英文别名: 1-[4-(4-nitro-benzylidenamino)-phenyl]-ethanone；1-[4-(4-Nitro-benzylidenamino)-phenyl]-aethanon；Ethanone, 1-[4-(4-nitrobenzylidenamino)phenyl]-；1-[4-[(4-nitrophenyl)methylideneamino]phenyl]ethanone
• CAS: 20534-89-8
• 化学式: C₁₅H₁₂N₂O₃
• mdl: MFCD00298909
• 分子量: 268.272
• InChiKey: BVABHWRNVARUQC-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  469.1±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Acetyl-N-(4-nitrobenzylidene)aniline 在 乙醇 、 sodium methylate 、 安息香精油 作用下， 生成 bis-{4-[(4-acetyl-phenylimino)-methyl]-phenyl}-diazene-N-oxide
  参考文献：
  名称：

  CCLXXV。-芳香族酮醇还原硝基化合物。第一部分。一些对-乙氧基化合物

  摘要：

  DOI：

  10.1039/jr9270002081
• 作为产物：
  描述：

  对硝基苯甲醛 、 4-氨基苯乙酮 在 溶剂黄146 作用下， 以 苯 为溶剂， 生成 4-Acetyl-N-(4-nitrobenzylidene)aniline
  参考文献：
  名称：

  作为 p38α 丝裂原激活蛋白激酶抑制剂的新型杂项查耳酮的设计、合成和分子对接

  摘要：

  合成并评估了新的查耳酮作为 p38-α 型丝裂原激活蛋白激酶 (MAPK) 抑制剂。据美国国家癌症研究所称，研究结果表明，在 10 μM 剂量下，化合物3a和6是所有测试化合物中活性最强的，平均生长抑制率分别为 94.83 和 58.49。在 5 剂量测试中，它们显示出微摩尔范围内的抗癌活性，GI 50分别在 1.41-46.1 和 2.07-31.3 μM 范围内。此外，与正常PCS-800-017相比，其具有强大的活性，特别是针对白血病细胞系，并且对癌细胞具有良好的选择性，选择性指数分别为12.41和23.77。化合物3a和6相应地抑制p38αMAPK，IC 50值为0.1462±0.0063和0.4356±0.0189μM。图3a显示对HL-60(TB)细胞的良好抑制并诱导HL-60(TB)细胞的细胞周期停滞在G2/M期。此外，与多柔比星相比，它使总细胞凋亡增加14.68倍，使caspase-3水平增加3

  DOI：

  10.1002/cbdv.202400077

文献信息

• Chemoselectivity in reactions of an α-diazo-β-diketone with some conjugative double-bond systems
  作者：Jiaxi Xu、Qihan Zhang、Liangbi Chen、Hui Chen

  DOI：10.1039/b103173m

  日期：——

  Reactions of 2-diazo-1,3-diphenylpropane-1,3-dione with α,β-unsaturated aldehydes and ketones, and keto-imines, in refluxing anhydrous toluene indicate that benzoyl(phenyl)ketene, which is generated by the thermal Wolff rearrangement of 2-diazo-1,3-diphenylpropane-1,3-dione, shows a pronounced tendency to form chemospecific [2 + 4] Diels–Alder adducts with the carbonyl group in α,β-unsaturated aldehydes and ketones, and the imine group in keto-imines. The reactivity in reactions of the α-diazo-β-diketone with these conjugative double-bond systems is CN > CO > CC. However, benzoyl(phenyl)ketene reacts with α,β-unsaturated imines to produce chemospecific [2 + 2] cycloadducts: β-lactams.

  2-二氮基-1,3-二苯基丙烯-1,3-二酮与α,β-不饱和醛和酮以及酮亚胺在回流无水甲苯中的反应表明，通过热的沃尔夫重排生成的苯甲酰（苯基）烯酮，显示出与α,β-不饱和醛和酮中的羰基及酮亚胺中的亚胺基形成化学特异性[2+4]戴尔斯-阿尔德加合物的显著倾向。α-二氮基-β-二酮与这些共轭双键体系的反应活性顺序为CN > CO > CC。然而，苯甲酰（苯基）烯酮与α,β-不饱和亚胺反应生成化学特异性[2+2]环加合物：β-内酰胺。
• New chalcones bearing isatin scaffold: synthesis, molecular modeling and biological evaluation as anticancer agents
  作者：Yousry A. Ammar、Eman A. Fayed、Ashraf H. Bayoumi、Rogy R. Ezz、Mansour S. Alsaid、Aiten M. Soliman、Mostafa M. Ghorab

  DOI：10.1007/s11164-017-3019-z

  日期：2017.12

  Derivatives of isatin have been reported to possess cytotoxic effects against different human carcinoma cell lines. A series of new isatin-linked chalcones was synthesized starting from isatin. Most of the newly synthesized compounds were screened for their in vitro anticancer activity against human breast (MCF-7), liver (HepG-2), and colon (HCT-116) cancer cell lines. All the tested compounds exhibited antitumor activity, with IC50 ranging from 2.88 to 62.88 μM in comparison to the reference drug used in this study, Imatinib. Compounds 2–5 were the most active, with IC50 ranging from 2.88 to 18.12 μM for the three cell lines, while compound 7b also showed moderate activity against HepG-2, MCF-7 and HCT-116 with IC50 13.95, 31.66 and 11.78 μM, respectively. Furthermore, compound 7d showed high activity against HepG-2 cells with IC50 12.84 μM. Compound 4 was shown to be the most potent against both HepG-2 and HCT-116 cell lines, while compound 2 is the most potent against MCF-7. The compounds were also screened for their cytotoxic activity against normal breast cell line MCF-12A, and were found to possess mild cytotoxicity. A docking study was performed for the most active compounds in this study, 2–5, inside the active site of CDK2. All the docked compounds have shown favorable binding interactions and energy scores. Compound 4 has proved to be the best in binding interactions and energy score. These findings may explain the cytotoxic activity of the target compounds. A novel series of isatin-linked chalcones was synthesized. The target compounds were evaluated for their cytotoxic activity towards human breast (MCF-7), liver (HepG-2), colon (HCT-116) cancer cell lines and (MCF-12A) normal breast cell line.

  已报告异靛蓝的衍生物对不同人类癌细胞系具有细胞毒性作用。以异靛蓝为起始材料合成了一系列新的异靛蓝连接查尔酮。大多数新合成的化合物在体外筛选了其对人类乳腺癌（MCF-7）、肝癌（HepG-2）和结肠癌（HCT-116）细胞系的抗癌活性。所有测试的化合物均表现出抗肿瘤活性，其IC50在2.88至62.88 μM之间，相较于本研究使用的对照药物伊马替尼。化合物2-5表现出最高活性，三种细胞系的IC50范围在2.88至18.12 μM之间，而化合物7b对HepG-2、MCF-7和HCT-116也显示出中等活性，IC50分别为13.95、31.66和11.78 μM。此外，化合物7d对HepG-2细胞表现出较高活性，IC50为12.84 μM。化合物4对HepG-2和HCT-116细胞系显示出最强的活性，而化合物2对MCF-7表现出最强活性。这些化合物还被筛选出对正常乳腺细胞系MCF-12A的细胞毒性活性，发现其具有轻微的细胞毒性。对本研究中最活跃的化合物2-5在CDK2活性位点进行了对接研究。所有对接的化合物均显示出良好的结合相互作用和能量评分。化合物4在结合相互作用和能量评分方面表现最佳。这些发现可能解释了目标化合物的细胞毒性作用。合成了一系列新型的异靛蓝连接查尔酮，评估了目标化合物对人类乳腺癌（MCF-7）、肝癌（HepG-2）、结肠癌（HCT-116）细胞系及正常乳腺细胞系（MCF-12A）的细胞毒性活性。
• Inhibitory potential of some chalcones on cathepsins B, H and L
  作者：Shweta Garg、Neera Raghav

  DOI：10.1039/c5ra12856k

  日期：——

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes such as degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis etc.

  卡特普辛是细胞内蛋白酶，已知参与多种生理过程，如降解细胞外蛋白、前激素加工、动脉粥样硬化进展等。
• CCLXXV.—The reduction of nitro-compounds by aromatic ketols. Part I. Some p-azoxy-compounds
  作者：Hugh Bryan Nisbet

  DOI：10.1039/jr9270002081

  日期：——
• Design, Synthesis, and Molecular Docking of Novel Miscellaneous Chalcones as p38α Mitogen‐Activated Protein Kinase Inhibitors
  作者：Mai M. Zeid、Osama M. El‐Badry、Salwa Elmeligie、Rasha A. Hassan

  DOI：10.1002/cbdv.202400077

  日期：2024.4

  and evaluated to serve as p38-α type of mitogen-activated protein kinase (MAPK) inhibitors. According to the National Cancer Institute, the findings indicated that at a 10 μM dosage, compounds 3a and 6 were the most active among all the compounds examined, with mean growth inhibition% of 94.83 and 58.49, respectively. In 5-dose testing, they showed anticancer activity in the micro-molar range with GI50

  合成并评估了新的查耳酮作为 p38-α 型丝裂原激活蛋白激酶 (MAPK) 抑制剂。据美国国家癌症研究所称，研究结果表明，在 10 μM 剂量下，化合物3a和6是所有测试化合物中活性最强的，平均生长抑制率分别为 94.83 和 58.49。在 5 剂量测试中，它们显示出微摩尔范围内的抗癌活性，GI 50分别在 1.41-46.1 和 2.07-31.3 μM 范围内。此外，与正常PCS-800-017相比，其具有强大的活性，特别是针对白血病细胞系，并且对癌细胞具有良好的选择性，选择性指数分别为12.41和23.77。化合物3a和6相应地抑制p38αMAPK，IC 50值为0.1462±0.0063和0.4356±0.0189μM。图3a显示对HL-60(TB)细胞的良好抑制并诱导HL-60(TB)细胞的细胞周期停滞在G2/M期。此外，与多柔比星相比，它使总细胞凋亡增加14.68倍，使caspase-3水平增加3